This is because prop stream pulls from public records which is sometimes updated because people do additions and stuff and don't get permits for their work. 

I majored in history at a public university and spent my 20s skiing out west.

I'm not an attorney and this is just my opinion.I suggest you talk with a good WI real property attorney.I suspect you'll want to make sure something codifying your equitable interest is recorded in the public records of the county where the property is located otherwise a third party who lends money to or obtains a judgment against the Vendor my have priority over your interest since they didn't have constructive notice of it.I don't know much about WI law but it may be the seller wants a land contract because if you default he may just need to record a notice of the breach to clear your interest from the record rather than having to bring a foreclosure action. 

If I knew of a secret spot, I wouldn't talk about it on a public forum and educate my competition.

Train is available always but also takes 2.5 hours and good luck getting around anywhere but Manhattan on Public transport.My plan is to buy a few more in the Hudson Valley and then eventually migrate down towards NYC to buy a larger multi family.

So how might I asses the health of smaller towns or cities etc?

Any advice to share publicly?

Zero chance I share suggestions on a public forum.  

Without knowing your profile it's hard to answer and there are too many possibilities and variables to cover every scenario so it's pointless to try without knowing your profile.https://www.rd.usda.gov/public...

@Yanto Njam that particular one was actually in the MLS so publicly listed